Between 2014 and 2016, Under Armour spent close to $1 billion to acquire makers of activity- and diet-tracking mobile apps. Many long-term employees questioned Plank's strategy and whether the company would produce a return on their investment. Plank spent hours in one-on-one conversations to try and persuade those employees. "It was important," Plank said, "that this not just be my decision. The strategy was a success, earning the company the world's largest digital health-and-fitness community, with 150 million users.
In November 2014, Plank pledged $25 million to the University of Maryland to be used for the proposed athletics and academic complex. The project has converted Cole Field House, the school's former basketball arena, into the football facility, a sports medicine center and student entrepreneurship lab. In 2015, Plank pledged $16 million to St. John's College High School in Washington, DC, to fund athletics, academics and entrepreneurship initiatives. Plank donated $1 million to the Archdiocese of Baltimore in 2016 to help 100 more children go to Catholic school.